The Mid Life Dating Files 2025

If there were a biography about you, what would the title be?

If I Ever Write a Biography…

If I ever write a biography, the title will absolutely be:

Christy, Unfiltered: Stories I Probably Shouldn’t Have Shared

And if you’re wondering if that’s dramatic, let me assure you — it is not.

It’s documentation.

Because my life is a collection of moments that probably should have stayed private… but where is the joy in that?

I say things before I think.

I volunteer before I process.

I commit before I calculate.

And I absolutely post before I reconsider.

But here’s the thing — I laugh at myself constantly. So why shouldn’t everyone else?

Laughter makes life better.

Why be negative when you can be positive?

Why frown when you can smile?

Why pretend you have it together when clearly, no one does?

Case in point: our cruise last week.

Now, my family cruises the way other families go to church. It is structured. It is ritual. It is competitive.

They gamble.

A lot.

Which means we get “free” drinks.

And by “free,” I mean they have earned those drinks with dedication and commitment.

So every night, they all sit in the music room next to the casino playing cards because the drinks are flowing.

There is just one small detail.

The bartenders cannot come into the music room to take drink orders.

Which means someone has to go back and forth to the bar.

Guess who that someone is?

You guessed it.

Me.

I am now the cruise bartender shuttle.

Back and forth. Back and forth. Memorizing everyone’s drinks.

And let me tell you something — the casino bartenders know us. They know exactly what we drink and how we drink it. They see me coming and just start lining them up.

But here’s the real challenge.

My mother’s Cosmopolitan.

If her cosmo is not sweet enough?

Oh.

I will be right back at that bar.

Not because I want to be.

Because she will hand it back to me with “the look.”

And the bartenders just laugh and say, “We’re so glad it’s you dealing with her and not us.”

That should tell you everything.

Try eating at a restaurant with her.

Her meal is ALWAYS wrong.

Always.

Meanwhile, I am a vegetarian — the person most likely to have something messed up — and my meal is NEVER wrong.

What is that?!

I am convinced she has a sign floating above her head that only restaurants can see:

“Test This One.”

It gets slightly embarrassing.

We’ve reached the point where the rest of us just make eye contact and roll our eyes under our eyelids so she can’t see.

It’s subtle. It’s strategic. It’s survival.

I do feel sorry for my dad.

But honestly? He’s adapted.

He has become the funniest, most sarcastic human being alive. He just sits there, makes one quiet comment under his breath, and carries on like he’s narrating a documentary.

I have to give him kudos.

He has earned them.

And then.

We get on the plane.

We’re sitting in Miami, headed home. I’m in the middle seat between Mom and Dad like I’m twelve years old again.

I ask Mom to open the window shade so I can look out.

She looks at me very seriously and says,

“You can’t open it. It’s a rule. It lets the light in.”

I blink.

“What rule?”

“It’s a Delta rule. All airlines. You’re not allowed to open the shade.”

I said, “Whaaaat?! That is not a rule. Where did you come up with that?”

She doubles down.

“I’ve flown more than you.”

Ma’am.

No.

Now listen — in my former married life, we had planes. Plural. We flew private. We flew commercial. We flew a lot.

I was NOT about to let her rewrite aviation policy in seat 18B.

So what do I do?

I turn airplane mode off.

Yes, I did.

Because now it’s personal.

I Google it.

And guess what?

It is absolutely NOT a rule. In fact, during takeoff and landing it’s often recommended that window shades be open so flight attendants can see the wings and engines and assess conditions outside.

I slowly turn my phone toward her.

Silence.

And let me tell you… she ignored me from Miami to Atlanta.

Would not speak.

Because she did not want the window open.

And she did not want to lose.

But I had receipts.

Google receipts.

This is my life.

Cruise bartender.

Cosmo negotiator.

Google fact-checker.

Family memory archivist.

Professional over-sharer.

Tiny arguments.

Big reactions.

Zero chill.

And I am writing it all down.

Because one day, these are the stories we will laugh about.

The casino runs.

The Cosmo drama.

The restaurant complaints.

The Great Window Shade Standoff of Miami 2026.

Life is short.

You only live once.

You might as well document it.

You might as well laugh.

You might as well smile instead of frown.

And if I have to be the one walking back and forth across a cruise ship with six drinks in my hands while negotiating the sweetness level of a Cosmopolitan?

Fine.

But I’m blogging about it.

And if it ends up in a book one day?

Well.

You were warned.

— Christy